(Trimethylsilylmethyl)lithium (TMSCH2Li) and other substituted alkylmetal reagents may be useful in a number of organic transformations, including, e.g., polymer initiation reactions, the Peterson Olefination reaction and deprotonation and/or halogen-metal exchange reactions involving pyridines.
However, one drawback with using substituted alkylmetal reagents, and particularly reagents such as TMSCH2Li is that they may have modest solubility in hydrocarbon solvents. For example, one molar solutions of TMSCH2Li in hexanes or pentane may be available, but even at this low concentration, the TMSCH2Li may readily crystallize out of solution if stored below room temperature. The resulting TMSCH2Li crystals may be relatively large, and so may clog dispensing apparatuses. Such crystals may also be relatively slow to redissolve in hydrocarbon solvents.
It is known that the solubility of substituted alkylmetal reagents may be improved by adding ether co-solvents. However, the stability of the alkylmetal reagents with ether co-solvents is not suitable for storage over extended periods of time.
As such, it would be desirable to be able to increase the concentration of substituted methylmetal reagents in hydrocarbon solutions. It would also be desirable for such solutions to remain stable for relatively long periods of time.